PRACTICAL ORGANIC CHEMISTRY
(3) With an aromatic hydrocarbon and a halogen derivative
of an aliphatic hydrocarbon or aromatic hydrocarbon .substi-
tuted in the side-chain, new hydrocarbons may be built up (see
Prep. 102, p. 214),
QI-I,. + CoIIr,Br = C,;Hfi.C2H, + IIBr.
C8H6 + ClCHo.CV.IIn ~ C,iII5.CII2.C,sHB + MCI,
3CfiHG + CI1C13 = CH(C(;II,)., + slid.
Anthracene has been, synthesised from tetrabromethane and
benzene by this method,
I Br ! CII ! Hr ! ,CIU
CVIL; 11., i ! ; iio:c(iii4 = ctin/ i X,c(in4 + 4iiBr.
' ; ~Hr ! CII Ur "i '
(4) Amides may be prepared by the use of chloroformamide,
CBH0 -I- CICONHo = CGHVCO.NH3 + ITC1.
The chloroformamide is obtained by passing HC1 gas over
heated cyanuric acid (Gattermann),
IIOCN + 1IC1 = Cl.CONIIo.
(5) Hydroxyaldehydes have been obtained indirectly by -the
use of the crystalline compound HCI.HCN (which hydrochloric
acid forms with hydrocyanic acid) acting upon a phenol ether,
Cfln,OCH8 + HCI.HCN =
The aldime is subsequently hydrolysed with dilute sulphuric
H20 = C0H4<
In addition to the Friedel-Crafts' reaction, the aromatic
ketones may be obtained by distilling the calcium salt of the